US5739140AExpiredUtility
Selected novel aryl acrylics
Est. expiryNov 3, 2015(expired)· nominal 20-yr term from priority
Inventors:William P. ClintonJim I. McloughlinAnita E. OtalJohn J. ParlowDennis Paul PhillionAjit S. Shah
C07D 249/08C07C 251/60C07D 333/24A01N 37/50C07D 239/52C07D 231/12A01N 43/50A01N 43/653A01N 43/10C07C 69/734A01N 43/54C07D 233/56C07C 251/48
41
PatentIndex Score
3
Cited by
21
References
69
Claims
Abstract
Novel compounds of Formula I and methods of making and using the compounds which are useful as fungicides, particularly in the agricultural field: <IMAGE> wherein C1 and C2 are carbon atoms which are part of an aromatic ring; W is alkoxyimino, alkoxymethylene or alkylthiomethylene; R1 is independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, wherein the alkyl or alkoxy are optionally substituted by halogen, and p is 0, 1, or 2; Z is -CH2-, -CH(OH)-, -CO-, -O-, -S-, NR2 wherein R2 is hydrogen or a lower aliphatic group, -CH2CH2-, -CH=CH-, <IMAGE> -CH2O-, -CH2S-, -CH2S(O)-, -OCH2-, -SCH2-, -S(O)CH2-, -CH2ON=C(R3)- or -CH=NB wherein B is -O-CO-, -N=CR3, or -CR3R4- wherein R3 and R4 are independently hydrogen or C1-C4 alkyl optionally substituted by halogen; A is an aromatic moiety having 1-2 aromatic rings connected linearly from Z to I1 wherein the aromatic rings are optionally connected to each other and to I1 in a linear manner with oxygen, nitrogen, or sulfur; q is 0 or 1. I1 is: <IMAGE> or an agronomically acceptable salt thereof.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. Compounds of Formula I: ##STR94## wherein C 1 and C 2 are carbon atoms which are part of an aromatic ring and are selected from the group consisting of phenyl and thienyl; W is alkoxyimino, alkoxymethylene or alkylthiomethylene; R 1 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, wherein the alkyl or alkoxy are optionally substituted by halogen, and p is 0, 1, or 2; Z is --CH 2 --, --CH(OH)--, --CO--, --O--, --S--, --NR 2 -- wherein R 2 is hydrogen or a lower aliphatic group, --CH 2 CH 2 --, --CH═CH--, ##STR95## --CH 2 O--, --CH 2 S--, --CH 2 S(O)--, --OCH 2 --, --SCH 2 --, --S(O)CH 2 --, --CH 2 ON═C(R 3 )-- or --CH═NB wherein B is --O--CO--, --N═CR 3 , or --O--CR 3 R 4 -- wherein R 3 and R 4 are independently hydrogen or C 1 -C 4 alkyl optionally substituted by halogen; A is an aromatic moiety having 1-2 aromatic rings connected linearly from Z to I 1 wherein the aromatic rings are optionally connected to each other and to I 1 in a linear manner with oxygen, nitrogen, or sulfur; wherein each aromatic ring is optionally independently substituted by R 10 groups; q is 1; I 1 is: ##STR96## wherein K, L, M, and Q are independently C or N with the proviso that not more than one or two of K, L, M or Q can be N at once and when K, L, M and Q are carbon each is optionally substituted by R 5 ; n is 1 or 2; and each R 5 and R 10 group is independently selected from the group consisting of (a) halogen, (b) lower aliphatic group optionally substituted by halogen or C 1 -C 4 alkoxy, (c) C 1 -C 4 alkoxy optionally substituted by halogen, (d) --CN, (e) --(Y 1 ) q .sbsb.1 C(═X)(Y 2 ) q .sbsb.2 R 8 , where; X is O or S, q 1 and q 2 are 0 or 1, Y 1 and Y 2 are independently selected from the group consisting of O, S, and --NR 8 ; each R 8 is independently selected from the group consisting of hydrogen and a lower aliphatic group optionally substituted by halogen or a C 1 -C 4 alkoxy group, wherein R 8 cannot be hydrogen if both q 1 and q 2 are 1 and Y 2 is O or S; (f) --S(O) r R 9 where r is 0, 1, or 2, wherein R 9 is a lower aliphatic group optionally substituted by halogen or a C 1 -C 4 alkoxy group or R 9 is an aryl group optionally substituted by halogen, a C 1 -C 4 alkoxy group, or a C 1 -C 4 alkyl group, (g) --Si(R 9 ) 3 , (h)--C(═NOCH 3 )CH 3 , or (i) aryl, aryloxy, arylthio, and arylamino optionally substituted by halogen, C 1 -C 4 alkoxy, or a lower aliphatic group optionally substituted by halogen or C 1 -C 4 alkoxy, u is an integer from 0 to 4 R 6 is halogen, hydroxy, C 1 -C 4 alkoxy, or a lower aliphatic group, optionally substituted with C 1 -C 4 alkoxy or halogen; s is 0, 1, or 2; and R is: ##STR97## wherein X is S or O; Y is a bond, oxygen, sulfur, or nitrogen carrying a hydrogen, a C 1 -C 4 alkyl group or a C 1 -C 4 alkoxy group; each R 7 is independently selected from the group consisting of hydrogen, and a lower aliphatic group optionally substituted by halogen, hydroxy, or a C 1 -C 4 alkoxy group; or an agronomically acceptable salt thereof.
2. The compound of claim 1 wherein W is alkoxyimino.
3. The compound of claim 2 wherein R is ##STR98## wherein X and Y are oxygen atoms and R 7 is methyl.
4. The compound of claim 2 wherein C 1 and C 2 form a phenyl group.
5. The compound of claim 4 wherein Z is --CH 2 ON═C(R 3 )--.
6. The compound of claim 5 wherein q=1, A is phenyl, and R 3 is methyl.
7. The compound of claim 6 wherein K, L, M, and Q are carbon atoms and n=1.
8. The compound of claim 6 wherein K, L, M, and Q are carbon atoms and n=1.
9. The compound of claim 4 wherein Z is --CH 2 O--.
10. Compounds of Formula I: ##STR99## wherein C 1 and C 2 are carbon atoms which are part of an aromatic ring and are selected from the group consisting of phenyl and thienyl; W is alkoxyimino; R 1 is independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, wherein the alkyl or alkoxy are optionally substituted by halogen, and p is 0; Z is --O--, --CH 2 O--, CH 2 ON═C(R 3 )-- or --CH═NB wherein B is --O--CR 3 R 4 -- wherein R 3 is methyl and R 4 is hydrogen; A is an aromatic moiety having 1 aromatic ring connected linearly from Z to I 1 wherein the aromatic ring is optionally connected to I 1 in a linear manner with oxygen wherein the aromatic ring is optionally substituted by a C 1 -C 4 alkyl group; q is 1; I 1 is: ##STR100## wherein K, L, M and Q are C, and each is optionally substituted by R 5 ; n is 1 or 2; and each R 5 group is independently selected from the group consisting of (a) halogen, (b) lower aliphatic group, and (c) C 1 -C 4 alkoxy; u is 0 or 1; R 6 is a lower aliphatic group; s is 0 or 1; and R is: ##STR101## wherein X is O; Y is oxygen or nitrogen carrying a hydrogen; each R 7 is a lower aliphatic group optionally substituted by hydroxy; or an agronomically acceptable salt thereof.
11. A compound of claim 10 wherein said aromatic ring is phenyl.
12. A compound of claim 11 wherein said aromatic ring is thienyl.
13. The compound of claim 9 wherein q=1 and A is phenyl.
14. The compound of claim 13 wherein K, L, M, and Q are carbon atoms and n=1.
15. The compound of claim 13 wherein K, L, M, and Q are carbon atoms and n=2.
16. The compound of claim 9 wherein q=1 and A is phenoxy.
17. The compound of claim wherein K, L, M, and Q are carbon atoms and n=1.
18. The compound of claim 17 wherein K, L, M, and Q are carbon atoms and n=2.
19. The compound of claim 4 wherein Z is --CH═NB.
20. The compound of claim 19 wherein q=1, A is phenyl, and B is --OCR 3 R 4 wherein R 3 is hydrogen and R 4 is methyl.
21. The compound of claim 20 wherein K, L, M, and Q are carbon atoms and n=1.
22. The compound of claim 3 wherein C 1 and C 2 form a thienyl group.
23. The compound of claim 22 wherein Z is --CH 2 ON═C(R 3 )--.
24. The compound of claim 23 wherein q=1, A is phenyl, and R 3 is methyl.
25. The compound of claim 24 wherein K, L, M, and Q are carbon atoms and n=1.
26. The compound of claim 24 wherein K, L, M, and Q are carbon atoms and n=2.
27. The compound of claim 22 wherein Z is --CH 2 O--.
28. The compound of claim 27 wherein q=1 and A is phenyl.
29. The compound of claim 28 wherein K, L, M, and Q are carbon atoms and n=1.
30. The compound of claim 2 wherein R is ##STR102## wherein X is an oxygen atom, Y is an --NH-- group, and R 7 is methyl.
31. The compound of claim 30 wherein C 1 and C 2 form a phenyl group.
32. The compound of claim 31 wherein Z is --CH 2 ON═C(R 3 )--.
33. The compound of claim 32 wherein q=1, A is phenyl, and R 3 is methyl.
34. The compound of claim 33 wherein K, L, M, and Q are carbon atoms and n=1.
35. The compound of claim 33 wherein K, L, M, and Q are carbon atoms and n=2.
36. The compound of claim 31 wherein Z is --CH 2 O--.
37. The compound of claim 36 wherein q=1 and A is phenyl.
38. The compound of claim 37 wherein K, L, M, and Q are carbon atoms and n=1.
39. The compound of claim 37 wherein K, L, M, and Q are carbon atoms and n=2.
40. The compound of claim 31 wherein Z is --CH═NB.
41. The compound of claim 40 wherein q=1, A is phenyl, and B is --OCR 3 R 4 wherein R 3 is hydrogen and R 4 is methyl.
42. The compound of claim 41 wherein K, L, M, and Q are carbon atoms and n=1.
43. The compound of claim 41 wherein K, L, M, and Q are carbon atoms and n n=2.
44. The compound of claim 30 wherein C 1 and C 2 form a thienyl group.
45. The compound of claim 44 wherein Z is --CH 2 ON═C(R 3 )--.
46. The compound of claim 45 wherein q=1, A is phenyl, and R 3 is methyl.
47. The compound of claim 46 wherein K, L, M, and Q are carbon atoms and n=1.
48. The compound of claim 46 wherein K, L, M, and Q are carbon atoms and n=2.
49. The compound of claim 44 wherein Z is --CH 2 O--.
50. The compound of claim 49 wherein q=1 and A is phenyl.
51. The compound of claim 50 wherein K, L, M, and Q are carbon atoms and n=1.
52. The compound of claim 2 wherein R is ##STR103## wherein X is an oxygen atom, Y is an --NH-- group, and R 7 is a lower aliphatic group optionally substituted with --OH.
53. The compound of claim 52 wherein C 1 and C 2 form a phenyl group.
54. The compound of claim 53 wherein Z is --CH 2 O--.
55. The compound of claim 54 wherein q=1 and A is phenyl.
56. The compound of claim 55 wherein K, L, M, and Q are carbon atoms and n=1.
57. The compound of claim 1 wherein W is alkoxymethylene.
58. The compound of claim 57 wherein R is ##STR104## wherein X and Y are oxygen atoms and R 7 is methyl.
59. The compound of claim 58 wherein C 1 and C 2 form a phenyl group.
60. The compound of claim 59 wherein Z is --CH 2 O--.
61. The compound of claim 60 wherein q=1 and A is phenyl.
62. The compound of claim 61 wherein K, L, M, and Q are carbon atoms and n=1.
63. The compound of claim 61 wherein K, L, M, and Q are carbon atoms and n=2.
64. The compound of claim 59 wherein Z is --O--.
65. The compound of claim 64 wherein q=1 and A is pyrimidinyloxyphenyl.
66. The compound of claim 65 wherein K, L, M, and Q are carbon atoms and n=1.
67. The compound of claim 65 wherein K, L, M, and Q are carbon atoms and n=2.
68. The composition for use as a fungicide comprising a fungicidally effective amount of a compound of Formula I of claim 1 together with an agronomically acceptable carrier.
69. A method of using the compound of claim 1 as a fungicidal agent comprising treatment with an effective amount of a compound of claim 1.Cited by (0)
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